Head of Artificial Intelligence

Space Dinosaurs is transforming how online retailers build, operate, and grow their businesses. Building on our established ecommerce engineering and optimization business, we're evolving into a scalable AI product company. Our product, Momentum, is an AI platform designed to replace the fragmented ecosystem of ecommerce agencies, CRO specialists, developers, analytics tools, and experimentation platforms. Momentum analyzes retail sites, identifies and prioritizes revenue opportunities, implements improvements, tests results, and continuously learns from outcomes. Our ambition goes beyond AI copilots and dashboards: we're building a self-improving system that turns intelligence into measurable business results. With deep ecommerce expertise, an established customer base, production experience with major retailers, and experienced founders, we're positioned to build something differentiated. We're looking for a technical leader to shape Momentum's intelligence, architecture, team, and future.

Role Overview 

We're seeking a deeply technical, product-minded Head of AI to own Momentum's core intelligence: Analyze, Recommend, and Learn. You'll lead product strategy and engineering execution, determining how Momentum understands retailers, generates high-value recommendations, and learns from experiments and deployments.

This is a hands-on builder-leader role, not a traditional executive or pure research position. You'll personally design, prototype, code, evaluate, and ship critical AI capabilities while recruiting and leading a lean, exceptional team. Working directly with our founders and collaborating with Build and Test engineering, you'll balance AI innovation, architecture, product priorities, customer outcomes, and technical execution. The role offers significant opportunity to expand as Momentum scales.

Essential Functions 

• Own AI and Product Strategy & Delivery: Lead the product vision, technical strategy, roadmap, and execution of Momentum's Analyze, Recommend, and Learn capabilities.
• Build the Intelligence Loop: Integrate site, customer, behavioral, and experimentation data to identify opportunities, generate explainable and prioritized recommendations, and continuously improve decisions through observed outcomes.
• Architect & Ship AI Systems: Personally design and implement LLM workflows, tool-using agents, retrieval and memory systems, structured data pipelines, feedback loops, evaluation frameworks, and supporting services.
• Develop Learning Capabilities: Leverage historical and ongoing A/B testing outcomes across merchants while accounting for data quality, privacy, customer boundaries, and uncertainty.
• Translate Data Into Value: Turn complex retail data and ambiguous business problems into actionable, trustworthy, measurable product experiences.
• Measure AI Performance: Establish offline and production evaluations covering recommendation quality, ranking, grounding, cost, latency, reliability, and revenue impact, distinguishing meaningful improvements from plausible outputs.
• Drive Technical Decisions: Evaluate build-versus-buy options, frontier APIs, open-weight models, fine-tuning, and traditional ML to select practical, scalable solutions.
• Collaborate Across Product & Engineering: Partner with Build and Test teams to connect recommendations with implementation, experimentation, attribution, and continuous learning.
• Engage Customers: Work directly with design partners and early customers to validate hypotheses, understand workflows, and iterate toward commercial value.
• Build & Lead the Team: Recruit, mentor, and lead high-performing engineers while remaining hands-on and establishing strong engineering standards, rapid feedback cycles, and disciplined production practices.
• Communicate Effectively: Clearly articulate technical tradeoffs, priorities, and progress to founders, colleagues, customers, and investors when appropriate.

Qualifications 

• Proven success building and shipping production AI products or systems, ideally within a frontier AI lab, applied AI startup, or similarly demanding environment.
• Deep practical expertise in foundation models, prompting, structured outputs, agents, orchestration, retrieval, evaluation, model adaptation, and current AI limitations.
• Strong software engineering skills, including independently designing, developing, reviewing, and operating production code and data-intensive systems.
• Strong product judgment, including MVP definition, prioritization, user discovery, technical tradeoffs, and measurable business outcomes.
• Experience leading technical teams or initiatives, with the ability to recruit and mentor engineers while remaining an individual contributor.
• Ability to operate across AI experimentation, architecture, UX, business metrics, and hands-on debugging.
• High agency, curiosity, pragmatism, adaptability, and comfort navigating early-stage ambiguity.
• Excellent communication, collaboration, and low-ego technical leadership.

Especially compelling, but not required: Experience with frontier model labs, early-stage AI-native startups, recommendation/ranking systems, experimentation and causal inference, sparse or heterogeneous feedback, ecommerce, retail analytics, or conversion optimization.

We value what you've built, how you think, and your ability to lead from the front far more than titles, degrees, employers, or years of experience.

Tools 

Our technology stack will evolve, and you'll help shape it. Relevant experience includes Python, TypeScript, cloud and data infrastructure, model APIs, open-weight models, agent frameworks, vector and relational databases, data pipelines, experimentation platforms, observability, and AI evaluation tools. Commerce platform and analytics experience is a plus, not a requirement.

What We Offer

• Startup Environment: A lean, fast-moving team where ownership, autonomy, and accountability are expected.
• High-Impact Work: Meaningful, hands-on work with direct visibility into outcomes and production impact.
• Top-Tier Clients: Opportunities to work with well-known, global brands and complex, real-world challenges.
• Competitive Compensation & Benefits: Market-aligned pay, comprehensive benefits, and bonus structures where applicable.
• Unlimited PTO: Flexible time off built on trust, ownership, and clear expectations.
• 100% Remote Work: Work from anywhere with a distributed, async-first team.
• Founder-Level Impact: Own Momentum's core intelligence and directly influence its product direction, architecture, and long-term differentiation.
• Real-World Learning Advantage: Leverage an established retailer network, first-party operating context, and real experimentation outcomes rather than relying solely on synthetic benchmarks.
• Build & Lead: Remain hands-on with code and models while building the team, technical foundation, and operating culture for scale.
• Ambitious Product Vision: Help replace fragmented retail services and software with a unified, self-improving AI platform, with meaningful opportunities for original thinking.
• Autonomy & Access: Work directly with founders in a fast-moving environment where decisions quickly translate into shipped products and customer results.

EEO Statement: Space Dinosaurs is an equal opportunity employer. We do not discriminate based on race, color, religion, sex, gender identity or expression, sexual orientation, national origin, age, disability, veteran status, or any other legally protected characteristic. Employment decisions are based on job-related qualifications and business needs.